The present invention is concerned with bis-esters of resorcinol (1,3-dihydroxybenzene) with ampicillin or amoxicillin and penicillanic acid 1,1-dioxide or 6-beta-(hydroxymethyl)penicillanic acid 1,1-dioxide, their utility as antibacterial agents, particularly via the oral route of administration, and intermediates therefor.
Ampicillin and amoxicillin are well-known members of the penicillin class of antibiotics, widely used in clinical practice. The beta-lactamase inhibitors, penicillanic acid 1,1-dioxide and 6-beta-(hydroxymethyl)penicillanic acid 1,1-dioxide represent more recent discoveries (Barth, U.S. Pat. No. 4,234,579 and U.K. Patent Application No. 2,061,930, respectively). The latter compounds find utility in enhancing the effectiveness of such beta-lactam antibiotics as ampicillin and amoxicillin, in particular extending the spectrum to bacterial organisms otherwise resistant to ampicillin or amoxicillin because of their production of beta-lactamase.
Even more recently ampicillin, amoxicillin and other penicillins have been combined with beta-lactamase inhibitors such as penicillanic acid 1,1-dioxide in the form of 1,1-alkanediol esters (e.g. Bigham, U.S. Pat. No. 4,244,951).